Solid-State Generation of Diarylisonaphthofuran and Its Mechanochemical Diels-Alder Reaction with Epoxynaphthalene

Chemistry. 2023 Dec 11;29(69):e202302660. doi: 10.1002/chem.202302660. Epub 2023 Nov 5.

Abstract

A solid-state method was developed for generating diarylisonaphthofurans from 1,3-diaryl-1,3-dihydronaphthofuranols. The generated reactive molecules were stable in the solid state and could be stored without any extra precautions. X-ray diffraction analysis revealed a typical quinoidal structure. Furthermore, the mechanochemical Diels-Alder reaction of 1,3-diarylisonaphthofurans with epoxynaphthalenes afforded synthetically attractive diepoxypentacenes.

Keywords: conjugated molecules; isonaphthofuran; mechanochemical Diels-Alder reactions; polycycle; reactive molecules.